US4101438A - Sulfonium compounds as corrosion inhibitors in aqueous acidic cleaning solutions - Google Patents

Sulfonium compounds as corrosion inhibitors in aqueous acidic cleaning solutions Download PDF

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Publication number
US4101438A
US4101438A US05/669,116 US66911676A US4101438A US 4101438 A US4101438 A US 4101438A US 66911676 A US66911676 A US 66911676A US 4101438 A US4101438 A US 4101438A
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sub
alkyl
carbon atoms
acid
composition defined
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Wayne W. Frenier
William J. Settineri
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Dow Chemical Co
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Dow Chemical Co
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Priority claimed from US05/386,652 external-priority patent/US3996147A/en
Priority claimed from CA180,820A external-priority patent/CA1005737A/en
Priority claimed from CA180,821A external-priority patent/CA1011230A/en
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    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
    • C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
    • C23G1/04—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors
    • C23G1/06—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors
    • C23G1/065—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors sulfur-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/12—Sulfonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/60—Sulfonium or phosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/02—Inorganic compounds
    • C11D7/04—Water-soluble compounds
    • C11D7/08—Acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/34—Organic compounds containing sulfur

Definitions

  • Iron oxide encrustations commonly known as rust or iron oxide scale, frequently form on ferrous metal surfaces.
  • Such surface deposits are objectionable on ferrous articles which are scheduled to be refinished (e.g. sheet steel) and are particularly troublesome when located on the surfaces of tubing and other conduits (e.g., boiling tubing, heat exchangers, connecting piping, and the like) wherein the deposits can restrict flow and interfere with heat exchange.
  • aqueous acidic cleaning solution e.g. aqueous HCl
  • An iron salt typically results from this operation, the specific salt depending upon the acidic cleaning medium used.
  • FeCl 3 and/or FeCl 2 are formed when HCl is used.
  • Such iron salts are generally soluble to at least a limited extent in the cleaning media. Ferric ions thus result.
  • Another object of this invention is to inhibit acid induced corrosion of ferrous metal surfaces even in the presence of ferric ions.
  • the sulfonium salts represented by I and II below are highly effective in inhibiting the corrosion of metals, particularly ferrous and cuprous metals, in contact with aqueous acid solutions.
  • the sulfonium salts correspond to the formula ##STR2## wherein n is 1 or 2; each R 1 independently is hydrogen or a hydrocarbyl, hydrocarbyloxy or hydrocarbylthio radical of from 1 to about 24 carbon atoms; R 2 is a hydrocarbyl or inertly-substituted hydrocarbyl radical of from 1 to about 24 carbon atoms, with the proviso that the total aggregate carbon content of R 1 and R 2 is from 7 to about 25; R 3 is an alkyl radical of from 1 to 4 carbon atoms or an inertly-substituted alkyl radical of from 2 to 4 carbon atoms, allyl, phenyl or an inertly-substituted phenyl radical; or R 2 and R 3 are joined to
  • the sulfonium salts represented by I and II are effective at low concentrations (e.g. 2 to 4 millimoles/liter) and are, surprisingly, effective even in the presence of ferric ions.
  • ferric ion corrosion problem experienced during the cleaning of ferrous metal surfaces can be substantially reduced if not eliminated by incorporating into the acidic cleaning solution a small but sufficient amount of said sulfonium salts to produce the desired inhibition effect.
  • Suitable sulfonium salts for use herein are represented by I and II above, each of which represents a known class of compounds. Such compounds are typically prepared in a known reaction comprising reacting a "benzyl" halide with an appropriate sulfide, as per the equation: ##STR3## In this illustration, of course, X is halogen (e.g. chloro or bromo) and becomes the anion (A.sup. ⁇ ) in the final product (I or II). The corresponding sulfonium salts containing other anions are then typically prepared by conventional ion-exchange techniques. Other methods of preparing I and II are known to those skilled in the art.
  • Suitable sulfonium salts are those in I and II wherein:
  • R 1 is hydrogen or a hydrocarbyl radical, such as alkyl (e.g. methyl, ethyl, propyl, butyl, hexyl, octyl, decyl, dodecyl, and the like), aryl (e.g. phenyl, naphthyl, and the like), aralkyl (e.g. benzyl, phenethyl, and the like), alkaryl (e.g. tolyl, 3,5-dimethylphenyl, butylphenyl, and the like), cycloalkyl (e.g. cyclohexyl and the like), alkenyl (e.g.
  • hydrocarbyloxy such as alkoxy, aryloxy, alkenyloxy, etc. (e.g. butoxy, phenoxy, p-hydroxyphenoxy, hexylphenoxy, chlorophenoxy, allyloxy, and the like); or hydrocarbylthio radicals, such as alkylthio, arylthio, etc. (e.g. methylthio, ethylthio, butylthio, phenylthio, and the like);
  • R 2 is a hydrocarbyl radical, such as alkyl (e.g. methyl, ethyl, propyl, butyl, hexyl, octyl, decyl, dodecyl, and the like), aryl (e.g. phenyl, hydroxyphenyl and the like), aralkyl (e.g. benzyl, phenethyl, phenylbutyl, and the like), alkaryl (e.g. tolyl, 3,5-dimethylphenyl, butylphenyl, hexylphenyl, and the like), cycloalkyl (e.g. cyclohexyl, and the like), alkenyl (e.g. allyl, butenyl, hexenyl, and the like; or
  • R 3 is an alkyl radical of from 1 to 4 carbon atoms (i.e. methyl, ethyl, propyl and butyl) or an inertly-substituted alkyl radical of 1 to 4 carbon atoms, allyl, phenyl or inertly-substituted phenyl.
  • inertly-substituted as used in this application is meant that the hydrocarbyl radical bears one or more substituents which are inert to the liquid acidic medium in which the sulfonium corrosion inhibitors are to be used. Such inert substituents include hydroxy, halo, etc.
  • R 3 includes hydroxyalkyl radicals of 1 to 4 carbon atoms, chloroalkyl radicals, and the like;
  • R 2 and R 3 can be joined to form, in combination with the sulfonium atom, a 5- or 6-membered heterocyclic ring (such as thiophenium, tetrahydrothiophenium, thiopyrylium and tetrahydrothiopyrylium);
  • A.sup. ⁇ is a compatible anion.
  • the choice of anion, A.sup. ⁇ is not critical and may be varied to convenience. However, the anion is generally chosen to be the same as the acid in solution as a matter of convenience.
  • the anion may be selected by the method of preparing the sulfonium salt or by ion exchange means. Examples of suitable anions include chloride, bromide, iodide, nitrate, bisulfate, tosylate, acetate, benzoate, dihydrogen phosphate, and the like.
  • R 1 is preferably a meta- or para-substituent (most preferably para) in I.
  • n 1 in I and II.
  • R 1 is preferably hydrogen, alkyl or alkylphenoxy and is most preferably alkyl of 8 to 18 carbon atoms.
  • R 2 is preferably alkyl, ⁇ -hydroxyalkyl of 2 to 4 carbon atoms (i.e. ⁇ -hydroxyethyl, ⁇ -hydroxypropyl and ⁇ -hydroxybutyl), allyl, phenyl or hydroxyphenyl, and is most preferably alkyl, ⁇ -hydroxyethyl or allyl.
  • R 3 is preferably alkyl of 1 to 4 carbon atoms, ⁇ -hydroxyalkyl of 2 to 4 carbon atoms, allyl, phenyl or hydroxyphenyl, and is most preferably alkyl of 1 to 4 carbon atoms, ⁇ -hydroxyethyl or allyl.
  • the preferred sulfonium salts are, of course, a combination of the above preferences for R 1 -R 3 and n.
  • the most preferred sulfonium salts are a combination of the most preferred embodiments for R 1 -R 3 with n being 1.
  • the sulfonium salts represented by Formula I are normally preferred over those represented by Formula II.
  • Suitable sulfonium salts for use herein include those in Formula I having the following values for R 1 -R 3 and A.sup. ⁇ . ##STR4##
  • the sulfonium compounds within Formula II having corresponding R 1 -R 3 and A.sup. ⁇ values are likewise representative compounds of the sulfonium salts within Formula II.
  • Other suitable compounds include the following: ##STR5## wherein n is 1 in each case and R 1 and A.sup. ⁇ have the following values:
  • the acid solutions suitable for use herein are aqueous solutions of non-oxidizing inorganic acids, such as HF, HCl, H 2 SO 4 , H 3 PO 4 , etc., and mixtures thereof (oxidizing inorganic acids include HNO 3 , HClO 4 , CrO 3 , etc.); or aqueous solutions of organic acids, such as formic acid acetic acid, sulfamic acid, hydroxy acetic, citric acid, etc., and mixtures thereof; or are aqueous solutions of known chelating agents, such as ethylenediaminetetraacetic acid, hereinafter EDTA (and the ammonium, amine, or alkali metal salts of EDTA), and other like polyaminepolycarboxylic acids and the like; and mixtures of such aqueous acid solutions.
  • non-oxidizing inorganic acids include HNO 3 , HClO 4 , CrO 3 , etc.
  • organic acids such as formic acid acetic acid,
  • the most common cleaning solutions are aqueous solutions of HCl and aqueous solutions of EDTA and amine or alkali metal salts of EDTA.
  • the acid solutions may be buffered to maintain a desired pH level with conventional buffering agents, such as citric acid, acetic acid, and salts thereof.
  • the pH values of acid cleaning solutions typically range from 1 to 5 for aqueous solutions of organic acids, and from pH 2-5 for aqueous solutions of chelating agents, such as the EDTA type cleaning solutions.
  • the normality of cleaning solutions using inorganic acids are typically greater than 1.
  • concentration of sulfonium salt used in the acid solutions may vary depending upon the particular salt, the particular metal and the degree of corrosion inhibition desired. Typically, concentrations of from about 1 ⁇ 10 -6 to about 0.1 moles of sulfonium salt per liter of solution are sufficient and concentrations of from about 1 ⁇ 10 -4 to 0.01 moles/liter are generally preferred.
  • Coupons of carbon steel having approximately 40 square centimeters of surface area were (a) scrubbed thoroughly with a soap-filled pad of steel wool in warm water, (b) rinsed with water, (c) washed with acetone, (d) pickled for 5 minutes in 10% aqueous HCl, (e) dried in air, and (f) weighed.
  • the coupons thus prepared were then suspended from glass hooks in a stirred acid cleaning solution at 25° C or 50° C for normally 16 hours; the coupons being completely immersed in the solution.
  • the coupons were then removed from the acid solutions, washed with soap and warm water, rinsed, dried and weighed.
  • the weight loss resulting from such treatment is a measure of corrosion.
  • the weight loss rate (WLR) having the units lbs./ft 2 /day is determined as follows: ##EQU1##
  • (a) 49.15 is a conversion factor for converting gm./cm. 2 /hr. to lbs./ft 2 /day;
  • the quantity of acid cleaning solution in each case was approximately 1400 milliliters.
  • Solution “A” was a 3.8 percent by weight, total weight basis, aqueous solution of an ammonium salt of ethylenediaminetetracetic acid buffered at a pH of 5 with citric acid and contained 0.10 percent by weight, total weight basis, of Fe +3 (added as FeNH 4 (SO 4 ) 2 ⁇ 12 H 2 O).
  • Solution “B” was a 10 percent by weight, total weight basis, aqueous solution of HCl, and 0.10 percent by weight of Fe +3 (added as FeCl 3 ).
  • Solution “C” was a 10 percent by weight, total weight basis, aqueous solution of H 2 SO 4 and 0.1 percent by weight of Fe +3 (added as FeNH 4 (SO 4 ) 2 ⁇ 12 H 2 O).
  • the R 1 radical was actually a mixture of C 8 -C 18 alkyl radicals with C 12 H 25 being the predominant species.
  • test solution "A” containing p-n-dodecylbenzyldimethylsulfonium chloride as the inhibitor was evaluated in a "flow test" wherein the solution was pumped through steel pipes for 6 to 7 hours and the degree of corrosion determined as above.
  • the steel pipes used in this test were sections cut from the same length of pipe and measured approximately 1 foot in length and 0.75 inch in inside diameter.
  • the pipes were cleaned free of rust by use of a commercial cleaning solution quite similar to solution "A” except that no Fe +3 was added, and were scrubbed with soap and warm water, rinsed with water, rinsed with acetone, dried and weighed. After the flow test, the pipes were again scrubbed, rinsed with water, rinsed with acetone, dried and weighed.
  • the subject sulfonium salts were evaluated as corrosion inhibitors in aqueous acid solutions which did not initially contain any significant amount of ferric ion.
  • Experiments 24 and 25 were conducted in 10 percent by weight, total weight basis, aqueous HCl solutions and experiment 26 was conducted in a 10 percent by weight aqueous H 2 SO 4 solution.
  • the inhibitor was p-dodecylbenzyldimethylsulfonium chloride and the metal coupons and the testing procedure used were substantially the same as described in experiments 1-10. The results are tabulated in Table VII below.
  • the concentration (Conc.) of sulfonium salt is expressed in millimoles per liter.
  • coupons cleaned with the test solutions inhibited with p-dodecylbenzyldimethylsulfonium chloride were observed to have a protective film of (predominantly) (p,p'-bisdodecyl)bibenzyl and p-dodecyltoluene on their surface; such coupons were suspended over water in a closed vessel for 11 days and showed only small localized rust spots while coupons cleaned with the uninhibited solutions and concurrently aged over water were uniformly covered with red rust.
  • the compounds used in experiments 46 and 47 are illustrative of sulfonium salts corresponding to the general formula ##STR11## wherein: R 2 and R 3 have the aforesaid meaning; R 4 is alkyl of 4 to about 20 carbon atoms; R 5 is methyl or ethyl; R 6 is hydrogen, methyl or ethyl; q is an integer of from 0 to 8; r is an integer of from 0 to 10; with the proviso that the sum of q plus r is equal to or less than 10.
  • Such compounds are conveniently prepared by reacting a xylyl dihalide (e.g.

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  • Chemical & Material Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Inorganic Chemistry (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
  • Detergent Compositions (AREA)
US05/669,116 1973-04-11 1976-03-22 Sulfonium compounds as corrosion inhibitors in aqueous acidic cleaning solutions Expired - Lifetime US4101438A (en)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
US35029573A 1973-04-11 1973-04-11
US05/386,652 US3996147A (en) 1971-02-23 1973-08-08 Novel sulfonium corrosion inhibitors in aqueous acid solutions
JP9448173A JPS5630398B2 (enrdf_load_stackoverflow) 1973-04-11 1973-08-24
GB4034473A GB1444171A (en) 1973-04-11 1973-08-24 Sulphonium salt corrosion inhibitors for aqueous acidic metal cleaning solutions rev
NLAANVRAGE7311808,A NL179147C (nl) 1973-04-11 1973-08-28 Werkwijze voor de bereiding van een zure reinigingsoplossing.
FR7331070A FR2245781B1 (enrdf_load_stackoverflow) 1973-04-11 1973-08-28
DE19732343382 DE2343382A1 (de) 1973-04-11 1973-08-28 Saure reinigungsloesungen
CA180,820A CA1005737A (en) 1973-04-11 1973-09-12 Sulfonium compounds as corrosion inhibitors in aqueous acidic cleaning solutions
CA180,821A CA1011230A (en) 1973-04-11 1973-09-12 Sulfonium corrosion inhibitors in aqueous acid solutions

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US06/011,745 Reissue USRE30283E (en) 1973-04-11 1979-02-13 Sulfonium compounds as corrosion inhibitors in aqueous acidic cleaning solutions

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US (1) US4101438A (enrdf_load_stackoverflow)
JP (1) JPS5630398B2 (enrdf_load_stackoverflow)
BE (1) BE804106A (enrdf_load_stackoverflow)
DE (1) DE2343382A1 (enrdf_load_stackoverflow)
FR (1) FR2245781B1 (enrdf_load_stackoverflow)
GB (1) GB1444171A (enrdf_load_stackoverflow)
NL (1) NL179147C (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4210552A (en) * 1973-04-11 1980-07-01 The Dow Chemical Company Sulfonium compounds as corrosion inhibitors in aqueous acidic cleaning solutions
US5190723A (en) * 1988-02-25 1993-03-02 Ciba-Geigy Corporation Process for inhibiting corrosion
US5587488A (en) * 1994-05-31 1996-12-24 The United States Of America As Represented By The Secretary Of The Navy Bis-sulfonium salts of amino substituted bis(halomethyl) benzene
US20090242422A1 (en) * 2008-03-31 2009-10-01 Kazuhiro Kurosu Method for recovering performance of electrolyzer for use in production of polysulfide and method for stopping holding electrolyzer

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3996147A (en) * 1971-02-23 1976-12-07 The Dow Chemical Company Novel sulfonium corrosion inhibitors in aqueous acid solutions

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL97745C (enrdf_load_stackoverflow) * 1957-05-14
US3668137A (en) * 1969-04-01 1972-06-06 Amchem Prod Composition and method for inhibiting acid attack of metals
DE2063987C3 (de) * 1970-12-28 1974-05-22 Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt Mittel und Verfahren zur Verhinderung der Korrosion von Eisen in saurer Lösung

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3996147A (en) * 1971-02-23 1976-12-07 The Dow Chemical Company Novel sulfonium corrosion inhibitors in aqueous acid solutions

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4210552A (en) * 1973-04-11 1980-07-01 The Dow Chemical Company Sulfonium compounds as corrosion inhibitors in aqueous acidic cleaning solutions
US5190723A (en) * 1988-02-25 1993-03-02 Ciba-Geigy Corporation Process for inhibiting corrosion
US5587488A (en) * 1994-05-31 1996-12-24 The United States Of America As Represented By The Secretary Of The Navy Bis-sulfonium salts of amino substituted bis(halomethyl) benzene
US20090242422A1 (en) * 2008-03-31 2009-10-01 Kazuhiro Kurosu Method for recovering performance of electrolyzer for use in production of polysulfide and method for stopping holding electrolyzer

Also Published As

Publication number Publication date
GB1444171A (en) 1976-07-28
FR2245781A1 (enrdf_load_stackoverflow) 1975-04-25
FR2245781B1 (enrdf_load_stackoverflow) 1976-05-07
NL7311808A (nl) 1975-03-04
NL179147B (nl) 1986-02-17
NL179147C (nl) 1986-07-16
DE2343382A1 (de) 1975-04-10
BE804106A (fr) 1974-02-28
JPS5630398B2 (enrdf_load_stackoverflow) 1981-07-14
JPS5045731A (enrdf_load_stackoverflow) 1975-04-24

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